(⿿)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

Lee, Sang‐Hyun; Lee, Hyun Woo; Sun, Ya Nan; Jang, Wonhee; Yang, Seo Young; Jang, Hae‐Dong; Kim, Young Ho

doi:10.1016/j.ijbiomac.2016.06.069

Cited by 25 publications

(11 citation statements)

References 23 publications

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“…Phenolic compounds from natural sources have shown anticholinesterase activity in several studies [ 34 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 ]. Phenolic compounds whose anticholinesterase activities have been reported are given in the Supplementary Material ( Table S2 ).…”

Section: Discussionmentioning

confidence: 99%

“…For those with prenyl groups ( 75 – 79 ) isolated from Maclura pomifera , there was no observable effect due to the presence of the prenyls, but an -OH group on ring B caused an increase in activity between compounds 75 and 76 . Catechin and its derivatives 79 to 84 isolated from Eugenia dysenterica and Orostachys japonicus had no good activity and no significant difference despite structural differences except between compound 82 and 83 where the additional benzoic acid substituent increased AChE and BChE inhibition activities [ 40 , 44 , 57 ]. This observation was similar for the flavanones 85 to 89 , though the addition of sugar molecules caused an increase in AChE and BChE inhibitions in compound 90 compared to compound 85 [ 50 , 51 , 56 , 64 ].…”

Section: Discussionmentioning

confidence: 99%

“…Compounds 39-41 have acetyl groups and their BChE inhibitory activity decreases with an increase in the number of acetyl groups [21]. The phenolic acid compounds 42-45, and compound 44 ferulic acid methyl ester have a good percentage of cholinesterase inhibition [17,18,57]. The presence of sugar substituents causes a decrease in cholinesterase inhibition as seen in compounds 46-48 [17,58], while an additional phenolic group causes an increase in cholinesterase inhibition as seen in compounds 49-64 [16,18,47,52,[59][60][61][62].…”

Section: Phenolic Compoundsmentioning

confidence: 99%

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Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

et al. 2021

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Alzheimer’s disease (AD) is a severe neurodegenerative disorder of different brain regions accompanied by distresses and affecting more than 25 million people in the world. This progressive brain deterioration affects the central nervous system and has negative impacts on a patient’s daily activities such as memory impairment. The most important challenge concerning AD is the development of new drugs for long-term treatment or prevention, with lesser side effects and greater efficiency as cholinesterases inhibitors and the ability to remove amyloid-beta(Aβ) deposits and other related AD neuropathologies. Natural sources provide promising alternatives to synthetic cholinesterase inhibitors and many have been reported for alkaloids while neglecting other classes with potential cholinesterase inhibition. This review summarizes information about the therapeutic potential of small natural molecules from medicinal herbs, belonging to terpenoids, coumarins, and phenolic compounds, and others, which have gained special attention due to their specific modes of action and their advantages of low toxicity and high efficiency in the treatment of AD. Some show superior drug-like features in comparison to synthetic cholinesterase inhibitors. We expect that the listed phytoconstituents in this review will serve as promising tools and chemical scaffolds for the discovery of new potent therapeutic leads for the amelioration and treatment of Alzheimer’s disease.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Phenolic Compoundsmentioning

confidence: 99%

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Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

et al. 2021

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“…Gromacs version 4.6.5 package was employed for the molecular dynamics (MD) simulation of tyrosinase and the tyrosinase–ligand complex. Molecular simulations were performed as described previously [ 24 , 25 ]. Tyrosinase was assigned by the Gromos96 43a1 force field for MD simulation.…”

Section: Methodsmentioning

confidence: 99%

Chemical Constituents from Apios americana and Their Inhibitory Activity on Tyrosinase

Kim

Kang

et al. 2018

Molecules

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The goal of this study was to identify phytochemicals with inhibitory activity against tyrosinase. Nine compounds 1–9 were isolated from the tubers of Apios americana. This is the first report of aromadendrin 5-methyl ether (1) being isolated from the Apios species. Among them, compounds 2 and 8 showed inhibitory activity toward tyrosinase. Based on a Dixon plot, the potential Ki values of competitive inhibitors 2 and 8 were calculated as 10.3 ± 0.8 µM and 44.2 ± 1.7 µM, respectively. An IC50 value of 13.2 ± 1.0 µM was calculated for the slow-binding inhibitor 2 after preincubation with tyrosinase. Additionally, the predicted binding sites between the receptor and ligand, as well as secondary structure changes, in the presence of 2 were examined by molecular simulation.

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“…The methanol extract of the roots of A. americana was progressively fractionated into n -hexane, chloroform, ethyl acetate, butanol, and water. Ethyl acetate fraction was subjected to open column chromatographies over silica gel, C-18, and sephadex LH-20, to obtain a new isoflavonoid, 5-methoxy-2,5,7,4′-tetrahydroxy-coumaronochromone ( 1 ), along with genestein ( 2 ) [ 5 , 13 ], 3′-methoxy-4′,5,7-trihydroxyisoflavone ( 3 ) [ 13 ], gerontoisoflavone A ( 4 ) [ 5 ], 5-methoxygenistein-7- O -glucoside ( 5 ) [ 3 ], 2′-hydroxygenistein-7- O -glucoside ( 6 ) [ 3 ], 2′-hydroxygenistein-7- O -gentibioside ( 7 ) [ 3 ], and 4-hydroxybenzoic acid ( 8 ) [ 14 ] ( Figure 1 ). The structures were elucidated by a comparison of 1D- and 2D-NMR, and HR-ESIMS data, with those reported previously.…”

Section: Resultsmentioning

confidence: 99%

Soluble Epoxide Hydrolase Inhibitory Activity of Components Isolated from Apios americana Medik

Kim

Kang

et al. 2017

Molecules

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A new compound 1, 5-methoxy-2,5,7,4′-tetrahydroxy-coumaronochromone, along with seven known compounds (2–8), were isolated from Apios americana using open column chromatography. Their structures were established based on an analysis of 1D and 2D NMR, and MS spectra. Among these, two compounds 1 and 2 showed inhibitory activity on soluble epoxide hydrolase (sEH) at a concentration below 50 μM. The respective competitive (1) and mixed (2) inhibitors were revealed to have Ki values of 21.0 ± 0.8 and 14.5 ± 1.5 μM, based on the Dixon plot. The potential inhibitor (2) was visually presented in a predicted binding pose in the receptor by molecular docking. Additionally, molecular dynamics were performed for a detailed understanding of their complex by Gromacs 4.6.5 package.

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(⿿)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

Cited by 25 publications

References 23 publications

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

Chemical Constituents from Apios americana and Their Inhibitory Activity on Tyrosinase

Soluble Epoxide Hydrolase Inhibitory Activity of Components Isolated from Apios americana Medik

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